62691-70-7Relevant articles and documents
Production process of 5-(3, 3-dimethylguanidino)-2-oxopentanoic acid
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Paragraph 0036-0041, (2020/07/02)
The invention discloses a production process of 5-(3,3-dimethylguanidino)-2-oxopentanoic acid. The 5-(3,3-dimethylguanidino)-2-oxopentanoic acid is prepared by connecting two fragments; the first fragment is prepared by the following steps: carrying out a substitution reaction on diethyl oxalate, serving as an initial raw material, and 1,4-butyrolactone to generate an intermediate 1, carrying outa ring-opening bromination reaction on the intermediate 1 and an acetic acid solution of hydrobromic acid to obtain an intermediate 2, and carrying out an esterification reaction on the intermediate 2and methanol to prepare an intermediate 3; and the second fragment is prepared by reacting N,N'-bis-BOC-1H-1-guanidinopyrazole serving as an initial raw material with a methanol solution of dimethylamine to obtain an intermediate 4. An alkylation substitution reaction on the intermediates 4 and 3 to prepare an intermediate 5, the intermediate 5 is deprotected to obtain an intermediate 6, and ester is hydrolyzed to obtain the target product. By establishing strict internal control standards for initial raw materials and intermediates and strictly controlling key process step parameters, the qualified product can be stably prepared in multiple batches.
Preparation of α,α-disubstituted α-amino acid derivatives via alkyl addition to α-oxime esters with organozinc species
Mitani, Michiharu,Tanaka, Yasunori,Sawada, Akihiko,Misu, Ayuko,Matsumoto, Yoshihiro
body text, p. 1383 - 1391 (2009/04/04)
An α-oxime ester derivative prepared via treatment of an acetylenedicarboxylate or an α-keto ester with hydroxylamine underwent C-alkylation to the C=N bond of the oxime group by a Lewis-acid-promoted reaction with a trialkylzincate or a dialkylzinc reagent. The O-N bond of the thus obtained adduct was reductively cleaved under hydrogenolysis in the presence of the Pd-C catalyst to afford an α-amino ester. Treatment of the oxime derivative prepared from methyl 5-bromo-2-oxopentanoate with the trialkylzincate gave an α-alkyl proline derivative via the addition reaction followed by the intramolecular attack upon a bromine-bearing carbon. The reaction of ethyl 4-oxo-2-pentynoate with hydroxylamine formed an isoxazole derivative by way of the intramolecular attack of an in situ-generated oxime to the carbonyl group. From this isoxazole derivative, ethyl 2-amino-4-oxo-2- pentenoate was given by the Pd-C-catalyzed hydrogenolysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Bicycloheptane substituted diamide and its congener prostaglandin analogs
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, (2008/06/13)
Bicycloheptane substituted amide prostaglandin analogs are provided having the structural formula STR1 wherein m is 0 to 4; A is --CH=CH-- or --CH2 --CH2 --; n is 1 to 5; Q is --CH=CH--, --CH2 --, STR2 or a single bond; R is CO2 H, CO2 alkyl, CO2 alkali metal, CO2 polyhydroxyamine salt, --CH2 OH, STR3 wherein R4 and R5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R4 and R5 being other than hydroxy and lower alkoxy; p is 1 to 4; R1 is H or lower alkyl; q is 1 to 12; R2 is H or lower alkyl; and R3 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, lower alkyl-S-, aryl-S-, arylalkyl-S-, STR4 (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
